7-cyano-4-methyl-5-nitrobenzimidazole | 269083-14-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 7-cyano-4-methyl-5-nitrobenzimidazole
• 英文别名: 7-methyl-6-nitro-3H-benzimidazole-4-carbonitrile
• CAS: 269083-14-9
• 化学式: C₉H₆N₄O₂
• 分子量: 202.172
• InChiKey: KOODEGQAZKLUMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  98.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-cyano-4-methyl-5-nitrobenzimidazole 在 钯 氢气 、 silica gel 、 乙酸乙酯 、 甲醇 、 6-Amino-7-methyl-1H-benzimidazole-4-carbonitrile 作用下， 以 甲醇 为溶剂， 反应 14.0h， 以to give rise to 5-amino-7-cyano4-methylbenzimidazole的产率得到6-Amino-7-methyl-1H-benzimidazole-4-carbonitrile
  参考文献：
  名称：

  Process for making 2-amino-2-imidazoline, guanidine and

  摘要：

  本发明提供了一种制备2-氨基-2-咪唑啉、鸟氨酸和2-氨基-3,4,5,6-四氢嘧啶衍生物的方法，该方法通过在两步反应中制备相应的活化2-硫代取代基2-衍生物，并在质子源的存在下进一步反应得到分离的衍生物与适当的胺或其盐。本方法允许在消除冗长、昂贵或多次低产率步骤和高毒性反应物的反应条件下制备2-氨基-2-咪唑啉、鸟氨酸和2-氨基-3,4,5,6-四氢嘧啶。该方法允许提高产率和产品纯度，并提供了额外的合成灵活性。

  公开号：

  US06066740A1
• 作为产物：
  描述：

  7-methyl-6-nitro-1H-benzimidazole-4-carboxamide 生成 7-cyano-4-methyl-5-nitrobenzimidazole
  参考文献：
  名称：

  5-(2-imidazolinylamino)-benzimidazole derivatives, their preparation and their use as .alpha.-adrenoceptor agonists with improved metabolic stability

  摘要：

  具有通用结构的苯并咪唑化合物：被用于治疗α-2介导的疾病，包括鼻塞、青光眼、哮喘、偏头痛和腹泻。

  公开号：

  US06486190B1

文献信息

• Process for making 2-amino-2-imidazoline, guanidine and
  申请人：The Procter & Gamble Company

  公开号：US06066740A1

  公开（公告）日：2000-05-23

  The present invention provides a process for making 2-amino-2-imidazoline, guanidine, and 2-amino-3,4,5,6-tetrahydroyrimidine derivatives by preparing the corresponding activated 2-thio-subsituted-2-derivative in a two-step, one-pot procedure and by further reacting yields this isolated derivative with the appropriate amine or its salts in the presence of a proton source. The present process allows for the preparation of 2-amino-2-imidazolines, quanidines, and 2-amino-3,4,5,6-tetrahydropyrimidines under reaction conditions that eliminate the need for lengthy, costly, or multiple low yielding steps, and highly toxic reactants. This process allows for improved yields and product purity and provides additional synthetic flexibility.

  本发明提供了一种制备2-氨基-2-咪唑啉、胍和2-氨基-3,4,5,6-四氢嘧啶衍生物的方法，通过在两步一锅程序中制备相应活化的2-硫代取代-2-衍生物，并进一步在质子源存在下将得到的孤立衍生物与适当的胺或其盐反应。本方法允许在消除了冗长、昂贵或多次低产率步骤以及高毒性反应物的反应条件下制备2-氨基-2-咪唑啉、胍和2-氨基-3,4,5,6-四氢嘧啶。该方法提高了产率和产品纯度，并提供了额外的合成灵活性。
• 5-(2-imidazolinylamino)-benzimidazole derivatives, their preparation and their use as .alpha.-adrenoceptor agonists with improved metabolic stability
  申请人：The Procter & Gamble Company

  公开号：US06486190B1

  公开（公告）日：2002-11-26

  Benzimidazole compounds having the generic structure: are used to treat alpha-2 mediated disorders, including nasal congestion, glaucoma, asthma, migraine, and diarrhea.

  苯并咪唑类化合物具有以下通用结构：用于治疗α-2介导的疾病，包括鼻塞、青光眼、哮喘、偏头痛和腹泻。
• [EN] 5-(2-IMIDAZOLINYLAMINO)-BENZIMIDAZOLE DERIVATIVES, THEIR PREPARATION AND THEIR USE AS .ALPHA.-ADRENOCEPTOR AGONISTS WITH IMPROVED METABOLIC STABILITY<br/>[FR] 5-(2-IMIDAZOLINYLAMINO)-BENZIMIDAZOLE, DERIVES ET PROCEDES DE PREPARATION ET D'UTILISATION DE CES DERNIERS EN TANT QU'AGONISTES DU RECEPTEUR ALPHA-ADRENERGIQUE AYANT UNE MEILLEURE STABILITE METABOLIQUE
  申请人：PROCTER & GAMBLE

  公开号：WO1999026942A1

  公开（公告）日：1999-06-03

  The present invention is directed to compounds having a structure according formula (I), wherein: (a) R1 is alkyl; (b) R2 is selected from the group consisting of: hydrogen, alkyl, methoxy, cyano, and halo; (c) R3 is selected from the group consisting of: hydrogen, methyl, hydroxy, cyano and halo; (d) R4 is selected from the group consisting of: hydrogen, methyl, ethyl and isopropyl; (e) R5 is selected from the group consisting of: hydrogen, methyl, amino, methoxy, hydroxy, cyano and halo; (f) provided that at least one of R2, R3, R4 or R5 is other than hydrogen or fluorine; (g) provided that when R1 is methyl and both R2 and R5 are hydrogen, R3 is other than methyl or halo; (h) provided that when R3 is cyano, R1 is methyl; and any tautomer of the structure or a pharmaceutically acceptable salt, or biohydrolyzable ester, amide, or imide thereof. The compounds of the present invention are peripherally acting selective alpha-2 adrenergic compounds that lower CNS activity and that resist metabolic transformation into undesirable compounds.

  本发明涉及具有以下式（I）的结构的化合物，其中：（a）R1是烷基；（b）R2选自以下组：氢，烷基，甲氧基，氰基和卤素；（c）R3选自以下组：氢，甲基，羟基，氰基和卤素；（d）R4选自以下组：氢，甲基，乙基和异丙基；（e）R5选自以下组：氢，甲基，氨基，甲氧基，羟基，氰基和卤素；（f）至少有一个R2，R3，R4或R5不是氢或氟；（g）当R1是甲基且R2和R5均为氢时，R3不是甲基或卤素；（h）当R3是氰基时，R1是甲基；以及该结构的任何互变异构体或药学上可接受的盐，或可生物水解的酯，酰胺或亚胺。本发明的化合物是周围作用的选择性α-2肾上腺素化合物，可以降低中枢神经系统的活性，并抵抗代谢转化为不良化合物。
• [EN] METHODS OF MAKING 6-[(4,5-DIHYDRO-1H-IMIDAZOL-2-YL)AMINO-]-7-METHYL-1H-BENZIMIDAZOLE-4-CARBONITRILE AND ITS PREFERRED SALT FORM<br/>[FR] PROCEDES DE FABRICATION DE 6-[(4,5-DIHYDRO-1H-IMIDAZOL-2-YL)AMINO-]-7-METHYL-1H-BENZIMIDAZOLE-4-CARBONITRILE ET FORME PREFEREE D'UN SEL DE CELUI-CI
  申请人：PROCTER & GAMBLE

  公开号：WO2004074279A1

  公开（公告）日：2004-09-02

  6-[(4,5-Dihydro-1H-imidazol-2-yl)amino-]-7-methyl-1H-benzimidazole-4-carbonitrile substantially free of 2,3,7-triamino-4,6-dimethyl-1,9-phenazinedicarbonitrile, and the anhydrous monoacetate salt thereof, are useful in the treatment of alpha-2 mediated disorders such as ocular hypertension.

  6-[(4,5-二氢-1H-咪唑-2-基)氨基]-7-甲基-1H-苯并咪唑-4-羧腈，基本上不含2,3,7-三氨基-4,6-二甲基-1,9-菲嗪二羧腈，以及其无水单乙酸盐，在治疗α-2介导的疾病，如眼压增高方面具有用处。
• Methods of making 6-[(4,5-dihydro-1H-imidazol-2-yl)amino-]-7-methyl-1H-benzimidazole-4-carbonitrile and its preferred salt form
  申请人：Randall Lynn Jared

  公开号：US20060122248A1

  公开（公告）日：2006-06-08

  6-[(4,5-Dihydro-1H-imidazol-2-yl)amino-]-7-methyl-1H-benzimidazole-4-carbonitrile substantially free of 2,3,7-triamino-4,6-dimethyl-1,9-phenazinedicarbonitrile, and the anhydrous monoacetate salt thereof, are useful in the treatment of alpha-2 mediated disorders such as ocular hypertension.

  6-[(4,5-二氢-1H-咪唑-2-基)氨基]-7-甲基-1H-苯并咪唑-4-羧腈，基本上不含2,3,7-三氨基-4,6-二甲基-1,9-苯并二氰基的盐酸单乙酰化物，可用于治疗α-2介导的疾病，如眼压增高。